organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 4| April 2010| Pages o854-o855

Bruceine A

aState Key Laboratory for Biology of Plant Diseases and Insect Pests, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, People's Republic of China
*Correspondence e-mail: hyjiang@ippcaas.cn

(Received 4 February 2010; accepted 1 March 2010; online 17 March 2010)

The title compound, C26H34O11, known as bruceine A, is a natural quassinoid extracted from the dried fruits of Brucea javanica. Its structure consists of five fused rings including an oxygen-containing heterocyclic ring and a lactone ring. Two intra­molecular O—H⋯O links help to establish the mol­ecular conformation. In the crystal, O—H⋯O hydrogen bonds connect the mol­ecules.

Related literature

For medicinal and pharmacological background to Brucea javanica and its extracts, see: Anderson et al. (1991[Anderson, M. M., O'Neill, M. J., Phillipson, J. D. & Warhurst, D. C. (1991). Planta Med. 57, 62-64.]); Bawm et al. (2008[Bawm, S., Matsuura, H., Elkhateeb, A., Nabeta, K., Subeki, Nonaka, N., Oku, Y., Katakura, K. (2008). Vet. Parasitol. 158, 288-294.]); Elkhateeb et al. (2008[Elkhateeb, A., Yamasaki, M., Maede, Y., Katakura, K., Nabeta, K. & Matsuura, H. (2008). Nat. Prod. Commun. 3, 145-148.]); Klocke et al. (1985[Klocke, J. A., Arisawa, M., Handa, S. S., Kinghorn, A. D., Cordel, I. G. A. & Farnsworth, N. R. (1985). Chem. Org. Naturst. 47, 222-264.]); Leskinen et al. (1984[Leskinen, V., Polonsky, J. & Bhatnagar, S. (1984). J. Chem. Ecol. 10, 1497-1507.]); Nakao et al. (2009[Nakao, R., Mizukami, C., Kawamura, Y., Subeki, Bawm, S., Yamasaki, M., Maede, Y., Matsuura, H., Nabeta, K., Nonaka, N., Oku, Y., Katakura, K. (2009). J. Vet. Med. Sci. 71, 33-41.]); O'Neill et al. (1987[O'Neill, M. J., Bray, D. H., Boardman, P., Chan, K. L., Phillipson, J. D., Warhurst, D. C. & Peters, W. (1987). J. Nat. Prod. 50, 41-48.]); Odjo et al. (1981[Odjo, A., Piart, J., Polonsky, J. & Roth, M. (1981). C. R. Acad. Sci. 293, 241-244.]); Pan et al. (2009[Pan, L., Chin, Y. W., Chai, H. B., Ninh, T. N., Soejarto, D. D. & Kinghorn, A. D. (2009). Bioorg. Med. Chem. 17, 2219-2224.]); Pavanand et al. (1986[Pavanand, K., Nutakul, W., Dechatiwongse, T., Yoshihira, K., Yongvanitchit, K., Scovill, J. P., Flippen-Anderson, J. L., Gilardi, R. & George, C. (1986). Planta Med. 52, 108-111.]); Subeki et al. (2007[Subeki, Matsuura, H., Takahashi, K., Nabeta, K., Yamasaki, M., Maede, Y., Katakura, K. (2007). J. Nat. Prod. 70, 1654-1657.]).

[Scheme 1]

Experimental

Crystal data
  • C26H34O11

  • Mr = 522.53

  • Orthorhombic, P 21 21 21

  • a = 9.0337 (12) Å

  • b = 10.167 (3) Å

  • c = 26.9122 (11) Å

  • V = 2471.8 (8) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.92 mm−1

  • T = 173 K

  • 0.44 × 0.30 × 0.14 mm

Data collection
  • Rigaku R-AXIS RAPID IP area-detector diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.687, Tmax = 0.882

  • 17108 measured reflections

  • 4478 independent reflections

  • 4051 reflections with I > 2σ(I)

  • Rint = 0.044

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.098

  • S = 1.13

  • 4478 reflections

  • 340 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.21 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1887 Friedel pairs

  • Flack parameter: −0.3 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2A⋯O9i 0.84 2.11 2.870 (3) 150
O2—H2A⋯O1 0.84 2.28 2.718 (3) 113
O5—H5A⋯O10ii 0.84 2.17 2.874 (2) 142
O5—H5A⋯O11 0.84 2.19 2.797 (2) 129
O6—H6A⋯O4iii 0.84 1.97 2.799 (3) 171
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) x+1, y, z.

Data collection: RAPID-AUTO (Rigaku, 2001[Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The bitter fruits of medicinal plant Brucea javanica (L.) Merr. Simaroubaceae is widely used in traditional medicine for various ailments (Bawm et al., 2008). Bruceine A, a natural quassinoid compound extracted from the fruits of B. javanica (L.) Merr., with a wide spectrum of biological effects, such as having potential antibabesial, antitrypanosomal, antimalarial and cytotoxicity against human cancer cell lines (Pan et al., 2009; Nakao et al., 2009; Elkhateeb et al., 2008; Subeki et al., 2007; Anderson et al.,1991; O'Neill et al.,1987; Pavanand et al.,1986). Bruceine A was also shown to have insecticidal, antifeedant, and growth inhibitory effects against the tobacco budworm, Heliothis virescens (F.), and the fall armyworm, Spodoptera frugiperda (Klocke et al., 1985), and strong antifeedant activity on the 3rd larvae of Locusta migratoria migratorioides R and F (Orthoptera, Acrididae) (Odjo et al.,1981) and the 4th instar larvae of Mexican bean beetle (Epilachna varivestis Mulsant) (Leskinen et al.,1984).

As part of our studies in this area, we have isolated the title compound (I), which has potential insecticidal activity against Spodoptera exigua (Lepidoptera: Noctuidae). The crystal structure of the title compound is shown in Fig. 1.

Related literature top

For medicinal and pharmacological background to Brucea javanica and its extracts, see: Anderson et al. (1991); Bawm et al. (2008); Elkhateeb et al. (2008); Klocke et al. (1985); Leskinen et al. (1984); Nakao et al. (2009); O'Neill et al. (1987); Odjo et al. (1981); Pan et al. (2009); Pavanand et al. (1986); Subeki et al. (2007).

Experimental top

The dried fruits of B. javanica were extracted with 80% ethanol for three days. Then the solution was filtered and removed into vacuo, and extracted with CHCl3 to give aqueous and CHCl3 layers. The CHCl3 layer was chromatographed on a silica gel column, and eluted successively with different MeOH–CHCl3 ratios. The MeOH–CHCl3 (20:80) eluate was evaporated to yield a residue, which was subjected to column chromatography on silica gel, eluted with hexane–EtOAc (50:50), to give the title compound (Bruceine A). The title compound was dissolved in acetone (20 ml) at room temperature, Colourless plates of (I) were obtained through slow evaporation after two weeks.

Refinement top

All the hydrogen atoms were placed at their geometrical positions (C—H = 0.93–0.98Å; O–H = 0.84Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C,O).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELX97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Ellipsoid plot.
(I) top
Crystal data top
C26H34O11F(000) = 1112
Mr = 522.53Dx = 1.404 Mg m3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54186 Å
Hall symbol: P 2ac 2abCell parameters from 657 reflections
a = 9.0337 (12) Åθ = 3.1–66.2°
b = 10.167 (3) ŵ = 0.92 mm1
c = 26.9122 (11) ÅT = 173 K
V = 2471.8 (8) Å3Plate, colourless
Z = 40.44 × 0.30 × 0.14 mm
Data collection top
Rigaku R-AXIS RAPID IP area-detector
diffractometer
4478 independent reflections
Radiation source: rotating anode4051 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
ω scans at fixed χ = 45°θmax = 68.2°, θmin = 3.3°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1010
Tmin = 0.687, Tmax = 0.882k = 1112
17108 measured reflectionsl = 3232
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044 w = 1/[σ2(Fo2) + (0.0199P)2 + 1.6367P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.098(Δ/σ)max < 0.001
S = 1.13Δρmax = 0.21 e Å3
4478 reflectionsΔρmin = 0.21 e Å3
340 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.00127 (11)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1887 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.3 (2)
Crystal data top
C26H34O11V = 2471.8 (8) Å3
Mr = 522.53Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 9.0337 (12) ŵ = 0.92 mm1
b = 10.167 (3) ÅT = 173 K
c = 26.9122 (11) Å0.44 × 0.30 × 0.14 mm
Data collection top
Rigaku R-AXIS RAPID IP area-detector
diffractometer
4478 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
4051 reflections with I > 2σ(I)
Tmin = 0.687, Tmax = 0.882Rint = 0.044
17108 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.098Δρmax = 0.21 e Å3
S = 1.13Δρmin = 0.21 e Å3
4478 reflectionsAbsolute structure: Flack (1983), 1887 Friedel pairs
340 parametersAbsolute structure parameter: 0.3 (2)
0 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.7087 (2)0.7346 (2)0.58066 (7)0.0362 (5)
O20.4645 (2)0.6705 (2)0.63450 (7)0.0372 (5)
H2A0.54790.69620.64440.056*
O30.1686 (2)0.4600 (2)0.42513 (6)0.0261 (5)
O40.0274 (2)0.5360 (2)0.36490 (7)0.0308 (5)
O50.5773 (2)0.64791 (18)0.32956 (6)0.0241 (4)
H5A0.56100.64360.29890.036*
O60.7799 (2)0.4626 (2)0.42098 (7)0.0292 (5)
H6A0.85950.47790.40600.044*
O70.6075 (2)0.29438 (18)0.35876 (6)0.0248 (5)
O80.2473 (2)0.51955 (19)0.29566 (6)0.0224 (4)
O90.1862 (2)0.73521 (19)0.29790 (7)0.0284 (5)
O100.4926 (2)0.26506 (19)0.26475 (6)0.0308 (5)
O110.5696 (2)0.47209 (19)0.24965 (6)0.0274 (5)
C10.6047 (4)0.6833 (3)0.55833 (10)0.0283 (7)
C20.4716 (3)0.6417 (3)0.58506 (10)0.0268 (6)
C30.3604 (3)0.5767 (3)0.56249 (10)0.0238 (6)
C40.3724 (3)0.5357 (3)0.50844 (9)0.0209 (6)
H4A0.31810.60350.48860.025*
C50.5338 (3)0.5333 (3)0.48864 (9)0.0200 (5)
C60.6068 (3)0.6646 (3)0.50295 (9)0.0237 (6)
H6B0.71040.66580.49090.028*
H6C0.55320.73800.48680.028*
C70.2220 (3)0.5461 (3)0.59057 (10)0.0306 (7)
H7A0.21390.60510.61920.046*
H7B0.22510.45470.60210.046*
H7C0.13620.55850.56880.046*
C80.6234 (3)0.4226 (3)0.51357 (10)0.0245 (7)
H8A0.61820.43240.54980.037*
H8B0.72690.42780.50280.037*
H8C0.58210.33710.50400.037*
C90.2980 (3)0.4027 (3)0.49735 (9)0.0256 (6)
H9A0.35390.33140.51390.031*
H9B0.19610.40290.51080.031*
C100.2930 (3)0.3772 (3)0.44191 (9)0.0202 (6)
H10A0.26400.28320.43690.024*
C110.4358 (3)0.4013 (3)0.41255 (9)0.0180 (6)
C120.5213 (3)0.5248 (3)0.43077 (8)0.0184 (5)
H12A0.45720.60090.42120.022*
C130.1512 (3)0.5072 (3)0.37875 (10)0.0241 (6)
C140.2882 (3)0.5266 (3)0.34730 (9)0.0204 (6)
H14A0.33580.61310.35490.024*
C150.3934 (3)0.4154 (3)0.35733 (9)0.0187 (6)
H15A0.34080.33260.34780.022*
C160.5477 (3)0.4080 (3)0.33405 (9)0.0208 (6)
C170.6442 (3)0.5287 (3)0.34586 (9)0.0221 (6)
H17A0.74280.51850.32940.026*
C180.6665 (3)0.5457 (3)0.40194 (9)0.0215 (6)
H18A0.69840.63870.40770.026*
C190.5370 (3)0.2805 (3)0.40671 (9)0.0224 (6)
H19A0.61210.27820.43350.027*
H19B0.47830.19830.40800.027*
C200.1948 (3)0.6338 (3)0.27507 (10)0.0228 (6)
C210.1545 (3)0.6143 (3)0.22154 (10)0.0286 (7)
H21A0.13140.52030.21580.034*
H21B0.24030.63770.20040.034*
C220.0221 (3)0.6972 (3)0.20635 (10)0.0318 (7)
H22A0.04420.79130.21430.038*
C230.1148 (4)0.6563 (5)0.23499 (13)0.0614 (12)
H23A0.09800.66960.27060.092*
H23B0.13560.56320.22860.092*
H23C0.19920.70970.22420.092*
C240.0041 (4)0.6853 (3)0.15038 (10)0.0406 (8)
H24A0.08460.71420.13250.061*
H24B0.08820.74070.14080.061*
H24C0.02550.59350.14200.061*
C250.5346 (3)0.3717 (3)0.27880 (9)0.0219 (6)
C260.5432 (4)0.4542 (3)0.19654 (9)0.0334 (7)
H26A0.54250.54020.18000.050*
H26B0.44740.41090.19160.050*
H26C0.62200.39960.18230.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0367 (13)0.0451 (13)0.0268 (11)0.0157 (11)0.0012 (10)0.0098 (10)
O20.0447 (13)0.0469 (13)0.0201 (10)0.0177 (12)0.0047 (10)0.0092 (10)
O30.0206 (10)0.0399 (12)0.0177 (10)0.0006 (9)0.0003 (8)0.0049 (9)
O40.0181 (10)0.0443 (12)0.0299 (11)0.0001 (10)0.0005 (9)0.0046 (10)
O50.0320 (11)0.0245 (10)0.0160 (9)0.0028 (9)0.0003 (8)0.0018 (8)
O60.0193 (10)0.0444 (13)0.0239 (10)0.0039 (10)0.0007 (8)0.0059 (10)
O70.0284 (11)0.0261 (11)0.0198 (10)0.0060 (9)0.0016 (8)0.0028 (8)
O80.0254 (10)0.0268 (10)0.0150 (9)0.0032 (9)0.0046 (8)0.0005 (8)
O90.0328 (12)0.0266 (11)0.0258 (10)0.0023 (10)0.0041 (9)0.0026 (9)
O100.0412 (13)0.0299 (11)0.0214 (10)0.0062 (10)0.0040 (9)0.0042 (8)
O110.0379 (12)0.0291 (10)0.0152 (9)0.0013 (10)0.0013 (8)0.0012 (8)
C10.0361 (18)0.0262 (16)0.0224 (15)0.0050 (14)0.0001 (13)0.0037 (12)
C20.0341 (16)0.0287 (15)0.0177 (13)0.0039 (14)0.0043 (13)0.0059 (12)
C30.0287 (16)0.0230 (14)0.0197 (14)0.0008 (12)0.0042 (12)0.0010 (11)
C40.0224 (14)0.0231 (14)0.0171 (13)0.0025 (13)0.0026 (11)0.0013 (12)
C50.0216 (13)0.0216 (13)0.0168 (12)0.0007 (13)0.0000 (11)0.0028 (11)
C60.0269 (16)0.0263 (15)0.0179 (13)0.0046 (13)0.0005 (12)0.0038 (12)
C70.0326 (16)0.0345 (17)0.0247 (15)0.0085 (15)0.0045 (13)0.0031 (13)
C80.0280 (16)0.0300 (16)0.0155 (13)0.0053 (13)0.0012 (12)0.0007 (12)
C90.0289 (15)0.0300 (16)0.0178 (14)0.0055 (14)0.0016 (12)0.0006 (12)
C100.0196 (14)0.0233 (15)0.0176 (13)0.0001 (12)0.0003 (11)0.0008 (11)
C110.0153 (13)0.0200 (13)0.0187 (13)0.0029 (11)0.0003 (11)0.0014 (11)
C120.0178 (13)0.0207 (13)0.0166 (12)0.0013 (12)0.0024 (11)0.0011 (11)
C130.0219 (14)0.0268 (15)0.0237 (14)0.0006 (13)0.0022 (11)0.0010 (12)
C140.0179 (13)0.0270 (15)0.0163 (13)0.0000 (13)0.0009 (10)0.0006 (12)
C150.0182 (13)0.0208 (14)0.0169 (13)0.0026 (12)0.0016 (11)0.0009 (11)
C160.0219 (14)0.0231 (14)0.0173 (13)0.0035 (12)0.0002 (11)0.0031 (11)
C170.0225 (14)0.0243 (14)0.0193 (14)0.0033 (13)0.0000 (11)0.0005 (12)
C180.0210 (14)0.0285 (15)0.0151 (13)0.0016 (13)0.0008 (11)0.0019 (12)
C190.0266 (15)0.0239 (14)0.0167 (13)0.0018 (13)0.0010 (12)0.0033 (11)
C200.0179 (14)0.0260 (15)0.0243 (14)0.0021 (12)0.0027 (12)0.0045 (12)
C210.0298 (16)0.0356 (17)0.0204 (14)0.0058 (15)0.0047 (12)0.0011 (13)
C220.0305 (16)0.0397 (17)0.0252 (15)0.0077 (15)0.0054 (13)0.0029 (13)
C230.030 (2)0.111 (4)0.043 (2)0.005 (2)0.0012 (16)0.010 (2)
C240.046 (2)0.046 (2)0.0298 (16)0.0170 (17)0.0123 (15)0.0003 (15)
C250.0223 (14)0.0244 (14)0.0191 (13)0.0011 (13)0.0032 (12)0.0013 (11)
C260.0490 (19)0.0343 (17)0.0169 (14)0.0012 (17)0.0033 (14)0.0016 (12)
Geometric parameters (Å, º) top
O1—C11.231 (3)C9—H9A0.9900
O2—C21.364 (3)C9—H9B0.9900
O2—H2A0.8401C10—C111.532 (3)
O3—C131.346 (3)C10—H10A1.0000
O3—C101.475 (3)C11—C191.539 (4)
O4—C131.215 (3)C11—C151.541 (3)
O5—C171.424 (3)C11—C121.554 (3)
O5—H5A0.8401C12—C181.539 (3)
O6—C181.423 (3)C12—H12A1.0000
O6—H6A0.8400C13—C141.512 (4)
O7—C161.438 (3)C14—C151.502 (4)
O7—C191.446 (3)C14—H14A1.0000
O8—C201.371 (3)C15—C161.530 (4)
O8—C141.440 (3)C15—H15A1.0000
O9—C201.203 (3)C16—C251.536 (3)
O10—C251.210 (3)C16—C171.539 (4)
O11—C251.325 (3)C17—C181.532 (3)
O11—C261.460 (3)C17—H17A1.0000
C1—C21.463 (4)C18—H18A1.0000
C1—C61.503 (3)C19—H19A0.9900
C2—C31.347 (4)C19—H19B0.9900
C3—C71.494 (4)C20—C211.499 (4)
C3—C41.517 (3)C21—C221.519 (4)
C4—C91.539 (4)C21—H21A0.9900
C4—C51.553 (4)C21—H21B0.9900
C4—H4A1.0000C22—C231.515 (4)
C5—C61.539 (4)C22—C241.529 (4)
C5—C81.540 (4)C22—H22A1.0000
C5—C121.564 (3)C23—H23A0.9800
C6—H6B0.9900C23—H23B0.9800
C6—H6C0.9900C23—H23C0.9800
C7—H7A0.9800C24—H24A0.9800
C7—H7B0.9800C24—H24B0.9800
C7—H7C0.9800C24—H24C0.9800
C8—H8A0.9800C26—H26A0.9800
C8—H8B0.9800C26—H26B0.9800
C8—H8C0.9800C26—H26C0.9800
C9—C101.515 (3)
C2—O2—H2A109.5O8—C14—C15107.4 (2)
C13—O3—C10125.2 (2)O8—C14—C13108.9 (2)
C17—O5—H5A109.5C15—C14—C13108.6 (2)
C18—O6—H6A109.5O8—C14—H14A110.6
C16—O7—C19109.04 (19)C15—C14—H14A110.6
C20—O8—C14115.9 (2)C13—C14—H14A110.6
C25—O11—C26116.4 (2)C14—C15—C16122.7 (2)
O1—C1—C2120.6 (2)C14—C15—C11113.6 (2)
O1—C1—C6121.8 (3)C16—C15—C1199.44 (19)
C2—C1—C6117.5 (2)C14—C15—H15A106.7
C3—C2—O2120.7 (3)C16—C15—H15A106.7
C3—C2—C1122.2 (2)C11—C15—H15A106.7
O2—C2—C1117.1 (2)O7—C16—C15101.1 (2)
C2—C3—C7119.9 (2)O7—C16—C25106.5 (2)
C2—C3—C4120.9 (2)C15—C16—C25109.8 (2)
C7—C3—C4119.2 (2)O7—C16—C17109.4 (2)
C3—C4—C9113.3 (2)C15—C16—C17113.1 (2)
C3—C4—C5113.6 (2)C25—C16—C17115.8 (2)
C9—C4—C5109.2 (2)O5—C17—C18105.3 (2)
C3—C4—H4A106.7O5—C17—C16112.0 (2)
C9—C4—H4A106.7C18—C17—C16111.6 (2)
C5—C4—H4A106.7O5—C17—H17A109.3
C6—C5—C8107.5 (2)C18—C17—H17A109.3
C6—C5—C4107.6 (2)C16—C17—H17A109.3
C8—C5—C4110.8 (2)O6—C18—C17112.5 (2)
C6—C5—C12109.2 (2)O6—C18—C12110.5 (2)
C8—C5—C12115.6 (2)C17—C18—C12111.6 (2)
C4—C5—C12105.9 (2)O6—C18—H18A107.3
C1—C6—C5110.6 (2)C17—C18—H18A107.3
C1—C6—H6B109.5C12—C18—H18A107.3
C5—C6—H6B109.5O7—C19—C11105.9 (2)
C1—C6—H6C109.5O7—C19—H19A110.5
C5—C6—H6C109.5C11—C19—H19A110.5
H6B—C6—H6C108.1O7—C19—H19B110.5
C3—C7—H7A109.5C11—C19—H19B110.5
C3—C7—H7B109.5H19A—C19—H19B108.7
H7A—C7—H7B109.5O9—C20—O8122.8 (2)
C3—C7—H7C109.5O9—C20—C21126.1 (3)
H7A—C7—H7C109.5O8—C20—C21111.1 (2)
H7B—C7—H7C109.5C20—C21—C22112.1 (2)
C5—C8—H8A109.5C20—C21—H21A109.2
C5—C8—H8B109.5C22—C21—H21A109.2
H8A—C8—H8B109.5C20—C21—H21B109.2
C5—C8—H8C109.5C22—C21—H21B109.2
H8A—C8—H8C109.5H21A—C21—H21B107.9
H8B—C8—H8C109.5C23—C22—C21110.7 (3)
C10—C9—C4110.8 (2)C23—C22—C24110.7 (3)
C10—C9—H9A109.5C21—C22—C24110.1 (2)
C4—C9—H9A109.5C23—C22—H22A108.5
C10—C9—H9B109.5C21—C22—H22A108.5
C4—C9—H9B109.5C24—C22—H22A108.5
H9A—C9—H9B108.1C22—C23—H23A109.5
O3—C10—C9103.1 (2)C22—C23—H23B109.5
O3—C10—C11113.1 (2)H23A—C23—H23B109.5
C9—C10—C11117.1 (2)C22—C23—H23C109.5
O3—C10—H10A107.7H23A—C23—H23C109.5
C9—C10—H10A107.7H23B—C23—H23C109.5
C11—C10—H10A107.7C22—C24—H24A109.5
C10—C11—C19115.2 (2)C22—C24—H24B109.5
C10—C11—C15107.7 (2)H24A—C24—H24B109.5
C19—C11—C1597.09 (19)C22—C24—H24C109.5
C10—C11—C12112.6 (2)H24A—C24—H24C109.5
C19—C11—C12112.4 (2)H24B—C24—H24C109.5
C15—C11—C12110.6 (2)O10—C25—O11125.5 (2)
C18—C12—C11112.1 (2)O10—C25—C16122.8 (2)
C18—C12—C5115.6 (2)O11—C25—C16111.7 (2)
C11—C12—C5113.3 (2)O11—C26—H26A109.5
C18—C12—H12A104.8O11—C26—H26B109.5
C11—C12—H12A104.8H26A—C26—H26B109.5
C5—C12—H12A104.8O11—C26—H26C109.5
O4—C13—O3118.6 (2)H26A—C26—H26C109.5
O4—C13—C14123.4 (2)H26B—C26—H26C109.5
O3—C13—C14118.0 (2)
O1—C1—C2—C3175.1 (3)O4—C13—C14—C15144.5 (3)
C6—C1—C2—C36.7 (4)O3—C13—C14—C1538.1 (3)
O1—C1—C2—O24.4 (4)O8—C14—C15—C1666.1 (3)
C6—C1—C2—O2173.8 (2)C13—C14—C15—C16176.3 (2)
O2—C2—C3—C75.4 (4)O8—C14—C15—C11174.3 (2)
C1—C2—C3—C7175.1 (3)C13—C14—C15—C1156.7 (3)
O2—C2—C3—C4175.6 (3)C10—C11—C15—C1459.6 (3)
C1—C2—C3—C43.9 (4)C19—C11—C15—C14178.9 (2)
C2—C3—C4—C9144.4 (3)C12—C11—C15—C1463.8 (3)
C7—C3—C4—C936.6 (4)C10—C11—C15—C16168.3 (2)
C2—C3—C4—C518.9 (4)C19—C11—C15—C1649.0 (2)
C7—C3—C4—C5162.1 (2)C12—C11—C15—C1668.3 (3)
C3—C4—C5—C649.3 (3)C19—O7—C16—C1527.3 (2)
C9—C4—C5—C6176.9 (2)C19—O7—C16—C25141.9 (2)
C3—C4—C5—C867.9 (3)C19—O7—C16—C1792.2 (2)
C9—C4—C5—C859.7 (3)C14—C15—C16—O7174.3 (2)
C3—C4—C5—C12166.0 (2)C11—C15—C16—O748.2 (2)
C9—C4—C5—C1266.4 (3)C14—C15—C16—C2573.5 (3)
O1—C1—C6—C5142.6 (3)C11—C15—C16—C25160.4 (2)
C2—C1—C6—C539.3 (4)C14—C15—C16—C1757.4 (3)
C8—C5—C6—C160.5 (3)C11—C15—C16—C1768.7 (3)
C4—C5—C6—C158.9 (3)O7—C16—C17—O5170.0 (2)
C12—C5—C6—C1173.4 (2)C15—C16—C17—O558.2 (3)
C3—C4—C9—C10171.4 (2)C25—C16—C17—O569.7 (3)
C5—C4—C9—C1060.9 (3)O7—C16—C17—C1852.3 (3)
C13—O3—C10—C9155.6 (2)C15—C16—C17—C1859.5 (3)
C13—O3—C10—C1128.2 (3)C25—C16—C17—C18172.6 (2)
C4—C9—C10—O378.0 (3)O5—C17—C18—O6157.1 (2)
C4—C9—C10—C1146.9 (3)C16—C17—C18—O681.1 (3)
O3—C10—C11—C19148.5 (2)O5—C17—C18—C1278.1 (3)
C9—C10—C11—C1991.8 (3)C16—C17—C18—C1243.7 (3)
O3—C10—C11—C1541.5 (3)C11—C12—C18—O680.7 (3)
C9—C10—C11—C15161.1 (2)C5—C12—C18—O651.2 (3)
O3—C10—C11—C1280.7 (3)C11—C12—C18—C1745.2 (3)
C9—C10—C11—C1238.9 (3)C5—C12—C18—C17177.1 (2)
C10—C11—C12—C18178.5 (2)C16—O7—C19—C114.5 (3)
C19—C11—C12—C1846.3 (3)C10—C11—C19—O7147.0 (2)
C15—C11—C12—C1861.0 (3)C15—C11—C19—O733.7 (2)
C10—C11—C12—C545.4 (3)C12—C11—C19—O782.2 (2)
C19—C11—C12—C586.8 (3)C14—O8—C20—O91.7 (4)
C15—C11—C12—C5165.9 (2)C14—O8—C20—C21179.4 (2)
C6—C5—C12—C1853.9 (3)O9—C20—C21—C2235.3 (4)
C8—C5—C12—C1867.3 (3)O8—C20—C21—C22145.8 (2)
C4—C5—C12—C18169.6 (2)C20—C21—C22—C2363.5 (4)
C6—C5—C12—C11174.7 (2)C20—C21—C22—C24173.9 (3)
C8—C5—C12—C1164.1 (3)C26—O11—C25—O105.2 (4)
C4—C5—C12—C1159.1 (3)C26—O11—C25—C16172.5 (2)
C10—O3—C13—O4156.4 (3)O7—C16—C25—O1040.6 (4)
C10—O3—C13—C1426.1 (4)C15—C16—C25—O1068.0 (3)
C20—O8—C14—C15158.5 (2)C17—C16—C25—O10162.5 (3)
C20—O8—C14—C1384.2 (3)O7—C16—C25—O11141.6 (2)
O4—C13—C14—O827.9 (4)C15—C16—C25—O11109.8 (3)
O3—C13—C14—O8154.7 (2)C17—C16—C25—O1119.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O9i0.842.112.870 (3)150
O2—H2A···O10.842.282.718 (3)113
O5—H5A···O10ii0.842.172.874 (2)142
O5—H5A···O110.842.192.797 (2)129
O6—H6A···O4iii0.841.972.799 (3)171
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x+1, y+1/2, z+1/2; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC26H34O11
Mr522.53
Crystal system, space groupOrthorhombic, P212121
Temperature (K)173
a, b, c (Å)9.0337 (12), 10.167 (3), 26.9122 (11)
V3)2471.8 (8)
Z4
Radiation typeCu Kα
µ (mm1)0.92
Crystal size (mm)0.44 × 0.30 × 0.14
Data collection
DiffractometerRigaku R-AXIS RAPID IP area-detector
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.687, 0.882
No. of measured, independent and
observed [I > 2σ(I)] reflections
17108, 4478, 4051
Rint0.044
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.098, 1.13
No. of reflections4478
No. of parameters340
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.21
Absolute structureFlack (1983), 1887 Friedel pairs
Absolute structure parameter0.3 (2)

Computer programs: RAPID-AUTO (Rigaku, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELX97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O9i0.842.112.870 (3)150
O2—H2A···O10.842.282.718 (3)113
O5—H5A···O10ii0.842.172.874 (2)142
O5—H5A···O110.842.192.797 (2)129
O6—H6A···O4iii0.841.972.799 (3)171
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x+1, y+1/2, z+1/2; (iii) x+1, y, z.
 

Acknowledgements

This work was supported by the Projects in the National Science & Technology Pillar Program in the Eleventh Five-year Plan Period (2006BAD08A03).

References

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Volume 66| Part 4| April 2010| Pages o854-o855
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